2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside
CAS No.:250740-58-0
Molecular Formula:C₂₇H₃₄O₁₄
Molecular Weight:582.559
Hs Code.:

Synonyms:2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

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Chemical Property of 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

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Technology Process of 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

There total 4 articles about 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

: 250740-57-9
ethyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside

: 250740-58-0
2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

Reference yield:

: 113893-72-4
2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

: 250740-58-0
2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂; tetrahydrofuran / 0.5 h / -40 °C

2: 87 percent / pyridine / 12 h

3: 76 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 6 h

4: 81 percent / trifluoromethanesulfonic acid; N-iodosuccinimide / CH₂Cl₂; tetrahydrofuran; H₂O

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; 1: Etherification / 2: Acetylation / 3: Ring cleavage / 4: Substitution;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

Reference yield:

: 250740-54-6
3,4-di-O-acetyl-β-L-rhamnopyranose 1,2-(ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranose-3-yl) orthoacetate

: 250740-58-0
2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / pyridine / 12 h

2: 76 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 6 h

3: 81 percent / trifluoromethanesulfonic acid; N-iodosuccinimide / CH₂Cl₂; tetrahydrofuran; H₂O

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; 1: Acetylation / 2: Ring cleavage / 3: Substitution;
DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k